How to Do It is Slate’s sex advice column. Send your questions to email@example.com. Don’t worry, we won’t use names.
Every Friday, Stoya and Rich will answer one bonus question in chat form. This week, sex never as good as with the ex.
Dear How to Do It,
My ex and I recently broke up. It was a very intense but short-lived relationship. Our sex life was out of this world. I’ve been putting myself out there again and have had a few sexual experiences, some better than others. The problem is, I had some of the best sex of my life with my ex, and all I can think about when having sex with literally anyone else is my ex. Everyone else pales in comparison. I’m scared that if I can’t have anything even close to a similar sexual compatibility, I’ll always feel like something is lacking. I had a horrible sex life with my husband of more than a decade, and I’m just not willing to go back to that. What should I do?
Rich: I think there are two ways to read this question: “Please tell me I’ll have sex that good again,” or “Please give me your blessing to start boning my ex again.”
Stoya: For the second, I’d want to know why they broke up.
Rich: Yes. But if she’s not dog-whistling her interest in getting back with her ex and is legitimately in search of good dick, I see this as a good problem to have. She can really just organize her quest for a mate around this desire and sample as she goes, as if the world were one big Sam’s Club where they serve penis on toothpicks. Prioritizing sexual performance isn’t unreasonable.
Stoya: So, I have some heterosexual insight.
Rich: Yes please!!!
Stoya: Finger-banging and oral sex are pretty crucial to most women’s orgasms. And if she was married for more than a decade—the bad sex during which seems like the real root of her fears—she might not have had a ton of experience on the dating circuit. So, select for skill from the available pool. Look for sexual partners who play a musical instrument with their hands (guitar, piano, trumpet) or are in detail-oriented or scientific fields professionally. I’m sure there are other groups with higher-than-average manual dexterity, focus, or problem-solving skills, but in my experience, those categories get you off to a good start.
Rich: I love it. Hands-on practicality. On the emotional side: Does it concern you at all that she’s fantasizing about her ex while she’s having sex with other guys?
Stoya: No, but maybe it should?
Rich: I’m of two minds. It seems dissociated and not ideal. At the same time, what gets you off gets you off. Ideally, the guy in front of her would be getting her off physically and mentally. She’s finding that rare. But I don’t think it’s an impossible thing to find, and it feels very possible she’s still just jonesing from a recent breakup, especially after having had bad sex for so long. Just as I don’t believe there’s only one perfect person for you (a soul mate), I don’t believe there’s one perfect sex partner for you (a … hole mate???).
Stoya: The dissociation angle is concerning, I agree. Some more dating with purpose, and sexual experimentation, might be the thing to try first. And I’m always pro-masturbation when something odd or frustrating is happening sexually.
Rich: Yeah, I think sometimes people have sexual problems that are just going to require fixes that aren’t quick. They’re going to have to undertake processes. The upside is that most of these processes involve getting laid, so they sound fun to me. And I don’t want to prescribe anything that gets in the way of her orgasms, but if I were her, I’d at least toy with the idea of weaning myself away from the fantasies about my ex, if at all possible. It was great, but try not to hold onto something you aren’t going back to. Unless you are going back to it, which will have its own complications.
Stoya: I say go all the way back to solo time until she can orgasm without thinking about the ex.
Rich: Reset it and forget it.
Stoya: Basically. Having sex when you’re not all the way there can get risky. And if you know how to get yourself off in the moment, and the sex isn’t working with whomever you’re with, you can walk away knowing you two just aren’t a fun match.
Rich: And just in case she is inching her way back toward the ex, and looking for our permission: “Very intense but short-lived” means reuniting for sex would almost certainly come with drama. And mere drama seems almost like the best-case scenario. The potential outcomes might be best delineated on a hot-sauce scale: It could be spicy; it could be nuclear; it could be ass in the tub.
Stoya: I mean, there’s a chance they’ll be able to meet for physical encounters without slipping into unhealthy routines, or losing workdays lost in each other’s big glossy eyes, or whatever the issue was.
Rich: I’m almost surprising myself to admit it, but I’ve never had sex with one of my exes. I mean, literally never! It’s always seemed like such a bad idea, and since New York is a reservoir of available, horny gay dudes, I’ve been able to distract myself in the event of temptation.
Stoya: I have. Sometimes someone’s heart gets rebroken, sometimes it’s great, sometimes the condom breaks and you’re standing in Walmart at 4:30 a.m. waiting to buy the morning-after pill.
Rich: All part of life’s adventure! I know this is extremely common—so much so that I feel like the weird one for not having experienced it. I think part of it has been circumstantial, but also I compartmentalize: You’re either in the bone zone or not, and you’re more likely to cross over from the literal dead than cross my arbitrarily designated lines.
Stoya: Why does revisiting ex sex seem like such a bad idea to you?
Rich: I guess I’m a pretty black-and-white kind of guy, so allowing things to linger in that gray area seems like torture. Someone’s going to get confused, and at least one party will be dissatisfied or disappointed soon enough. The baggage has always worried me. I’m not even into carry-on bags. I’ve had plenty of encounters with strangers and buddies that are blissfully devoid of emotion, but it just seems like the probability for caught and/or re-caught feelings is much higher with an ex. Life is complicated enough without making decisions that could very well complicate it further. But I know I’m an outlier and also obnoxiously careful.
Stoya: I’m having a deep-realization moment in response to your line about complication.
Rich: I hope it’s not salting a scar in any way!
Stoya: Not at all. I’m all, “Oh. Right. I can choose to avoid complication where possible. Amazing.”
Rich: Well, easier said than done. I’m kind of being a robot here, tbh.
Stoya: The baggage and heightened likelihood of emotion are real, so if she’s going to approach this person about becoming sexual together again, she needs to be really clear on what she wants and communicate directly about it.
Rich: Yes, and as much as possible, stick to that plan. Otherwise, she could be sentencing herself to limbo.
Stoya: That’s definitely how the broken hearts happen. In the meantime, whatever the case: masturbate.